Concentrated plant-protection formulation

Abstract

The current invention relates to a concentrated plant-protection formulation, comprising : a solvent according to formula (A), wherein R1 is selected from a C5 to C12 alkyl, as a solvent in a composition comprising a pesticide; and an active plant-protection product. The invention further relates to use of the formulation, for preparing a composition diluted in water of the active plant-protection product, by mixing at least one part by weight of concentrated formulation with at least 10 parts and preferably less than 1000 parts of water.

Description

[0001] CONCENTRATED PLANT-PROTECTION FORMULATION

[0002] FIELD OF THE INVENTION

[0003] The invention relates to a concentrated phytosanitary formulation containing an active ingredient. The composition includes more ecological solvents. It is stable and can be readily used by farmers. The present invention also relates to a solvent composition useful and essentially preferred for preparing the phytosanitary formulation.

[0004] BACKGROUND

[0005] Agriculture uses many active materials such as fertilizers or pesticides, for example insecticides, herbicides or fungicides. We are talking about active phytosanitary products (or active ingredients). Active phytosanitary products are generally produced in pure or highly concentrated form. They should be used on farms at low concentrations. To this end, they are generally formulated with other ingredients in order to allow easy dilution by weight by the farmer. We are talking about phytosanitary formulations. The dilution carried out by the farmer is generally carried out by mixing the phytosanitary formulation with water.

[0006] Thus the phytosanitary formulations must allow easy dilution by weight by the farmer, in order to obtain a product in which the phytosanitary product is correctly dispersed, for example in the form of a solution, emulsion, suspension, or suspension, emulsion. Phytosanitary formulations thus allow the transport of a phytosanitary product in relatively concentrated form, easy packaging and / or easy handling for the end user. Different types of phytosanitary formulations can be used according to the different phytosanitary products. Mention is made, for example, of emulsifiable concentrates (Emulsifiable Concentrates "EC"), concentrated emulsions (Emulsion in water "EW"), microemulsions ("ME"), wettable powders (Wettable Powders "WP"), granules dispersible in water (Water Dispersible Granules, "WDG").

[0007] Several prior art documents describe agrochemical formulations comprising dioxolane-based solvents, including WO2023 / 094567, WO2023 / 144370, EP3603398 and W02013 / 153030. These disclosures focus primarily on solvent systems containing protic dioxolane derivatives, such as 2,2-dimethyl-l,3-dioxolane-4- methanol (glycasol) and related hydroxy-functional compounds. The formulations in these documents are typically optimized for compatibility with aqueous media, and for the solubilization or dispersion of plant-protection actives that are at least partially hydrophilic or compatible with hydrogen-bond donating solvents. A shared limitation of these prior art disclosures is that they do not address the solubilization of plant-protection actives that require non-polar or aprotic environments, such as triazoles, dinitroanilines, strobilurins, or pyridate. These active ingredients are typically incompatible with protic solvents like glycasol and are therefore conventionally formulated in aromatic solvents such as xylene or Solvesso. While such solvents may serve as substitutes for earlier polar protic solvents such as glycols, they do not address the formulation challenges associated with replacing aprotic or aromatic solvents. The formulations that can be used depend on the physical form of the phytosanitary product (for example solid or liquid), and on its physico-chemical properties in the presence of other compounds such as water or solvents.

[0008] After dilution by weight by the farmer, for example by mixing with water, the phytosanitary product can be found in different physical forms: solution, dispersion of solid particles, dispersion of droplets of the product, droplets of solvent in which the product is dissolved... Phytosanitary formulations generally include compounds that make it possible to obtain these physical forms. They may, for example, be surfactants, solvents, mineral carriers and / or dispersants. Very often these compounds do not have an active character, but a character of an intermediate aid to the formulation. It is therefore very often desired to limit the quantity in order to limit the costs and / or a possible harmfulness for the environment. The phytosanitary formulations can in particular be in liquid form, or in solid form.

[0009] In order to prepare phytosanitary formulations of solid active phytosanitary products, it is known to dissolve the product in a solvent. The phytosanitary formulation thus comprises a solution of the product in the solvent. The formulation can be in solid form, for example in the form of a wettable powder (WP) where the solution impregnates an inorganic carrier, for example kaolin and / or silica. The formulation can alternatively be in liquid form, for example in the form of an emulsifiable concentrate (EC) having a single clear liquid phase comprising the solvent and the product in solution, which can form an emulsion by adding water, without stirring or with a low hustle. It can also be or in the form of a cloudy concentrated emulsion (EW), the phase of which dispersed in water comprises the solvent and the product in solution in the solvent. It can also be in the form of a clear microemulsion (ME), the phase of which dispersed in water comprises the solvent and the product in solution in the solvent. Some solid phytosanitary actives are often difficult to formulate. For example, tebuconazole is a particularly effective fungicide, and widely used, in particular for the cultivation of soybeans. For certain phytosanitary active ingredients, it is difficult to produce concentrated formulations that are easy to dilute for the farmer, stable, and without substantial disadvantages (proven or perceived) in terms of safety, toxicity and / or eco-toxicity. For some actives, it is difficult to formulate at relatively high concentrations, with sufficient stability.

[0010] In particular, it is necessary to avoid the appearance of crystals, in particular at low temperature and / or during dilution and / or during storage at high temperature of the diluted composition. The crystals can have negative effects, including clogging the filters of the devices used to dispense the diluted composition, clogging the spray devices, decreasing the overall activity of the formulation, creating unnecessary problems with waste streams to remove the crystals, and / or cause poor distribution of the active product on the agricultural field.

[0011] In particular, there is need for aprotic solvents which can substitute aromatic solvents currently used in concentrated phytosanitary formulations, such as naphthalene, depleted naphthalene, dimethylacetamide, cyclohexanone, benzyl alcohol, acetophenone, gamma butyrolactone, and N-methyl-2-pyrrolidone (NMP). These solvents have a known list of disadvantages, particularly a high environmental impact, toxicity concerns and their non-renewable nature. These issues have lead to an increase in regulatory restrictions.

[0012] However, their continued use in agriculture is driven by their effectiveness and versatility in formulating stable concentrated phytosanitary formulations. There remains a need to finding and adopting safer and more sustainable alternatives in particular for aprotic solvents.

[0013] SUMMARY OF THE INVENTION

[0014] The present invention and embodiments thereof serve to provide a solution to one or more of above-mentioned disadvantages. To this end, the present invention relates to a concentrated plant-protection formulation according to claim 1.

[0015] Preferred embodiments of the device are shown in any of the claims 2 to 14. Specific preferred embodiments of the solvent utilized in the plant-protection formulation relates to an invention according to claims 2 to 7. Specific preferred embodiments of the plant-protection product relate to an invention according to claims 12 to 14. The inventors have found that these preferred compounds can be adequately stabilized in the preferred solvents, allowing the formation of highly concentrated, stable phytosanitary formulations.

[0016] In a second aspect, the present invention relates to a use according to claim 15.

[0017] DETAILED DESCRIPTION OF THE INVENTION

[0018] The present invention concerns a concentrated plant-protection formulation.

[0019] Unless otherwise defined, all terms used in disclosing the invention, including technical and scientific terms, have the meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. By means of further guidance, term definitions are included to better appreciate the teaching of the present invention.

[0020] As used herein, the following terms have the following meanings:

[0021] "A", "an", and "the" as used herein refers to both singular and plural referents unless the context clearly dictates otherwise. By way of example, "a compartment" refers to one or more than one compartment.

[0022] "About" as used herein referring to a measurable value such as a parameter, an amount, a temporal duration, and the like, is meant to encompass variations of + / - 20% or less, preferably + / -10% or less, more preferably + / -5% or less, even more preferably + / -1% or less, and still more preferably + / -0.1% or less of and from the specified value, in so far such variations are appropriate to perform in the disclosed invention. However, it is to be understood that the value to which the modifier "about" refers is itself also specifically disclosed.

[0023] "Comprise", "comprising", and "comprises" and "comprised of" as used herein are synonymous with "include", "including", "includes" or "contain", "containing", "contains" and are inclusive or open-ended terms that specifies the presence of what follows e.g. component and do not exclude or preclude the presence of additional, non-recited components, features, element, members, steps, known in the art or disclosed therein.

[0024] Furthermore, the terms first, second, third and the like in the description and in the claims, are used for distinguishing between similar elements and not necessarily for describing a sequential or chronological order, unless specified. It is to be understood that the terms so used are interchangeable under appropriate circumstances and that the embodiments of the invention described herein are capable of operation in other sequences than described or illustrated herein.

[0025] The recitation of numerical ranges by endpoints includes all numbers and fractions subsumed within that range, as well as the recited endpoints.

[0026] The expression "% by weight", "weight percent", "%wt" or "wt%", here and throughout the description unless otherwise defined, refers to the relative weight of the respective component based on the overall weight of the formulation.

[0027] Whereas the terms "one or more" or "at least one", such as one or more or at least one member(s) of a group of members, is clear per se, by means of further exemplification, the term encompasses inter alia a reference to any one of said members, or to any two or more of said members, such as, e.g., any >3, >4, >5, >6 or >7 etc. of said members, and up to all said members.

[0028] Unless otherwise defined, all terms used in disclosing the invention, including technical and scientific terms, have the meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. By means of further guidance, definitions for the terms used in the description are included to better appreciate the teaching of the present invention. The terms or definitions used herein are provided solely to aid in the understanding of the invention.

[0029] Reference throughout this specification to "one embodiment" or "an embodiment" means that a particular feature, structure or characteristic described in connection with the embodiment is included in at least one embodiment of the present invention. Thus, appearances of the phrases "in one embodiment" or "in an embodiment" in various places throughout this specification are not necessarily all referring to the same embodiment, but may. Furthermore, the particular features, structures or characteristics may be combined in any suitable manner, as would be apparent to a person skilled in the art from this disclosure, in one or more embodiments. Furthermore, while some embodiments described herein include some but not other features included in other embodiments, combinations of features of different embodiments are meant to be within the scope of the invention, and form different embodiments, as would be understood by those in the art. For example, in the following claims, any of the claimed embodiments can be used in any combination.

[0030] The term "concentrated phytosanitary formulation" or "concentrated plantprotection formulation" or "concentrated phytosanitary composition" or "concentrated plant-protection composition" is understood to mean a formulation intended to be mixed with water (for example diluted) by the user, as opposed to a diluted phytosanitary composition.

[0031] The term "diluted phytosanitary composition" or "diluted plant-protection formulation" or "diluted phytosanitary composition" or "diluted plant-protection composition" is understood to mean a formulation which was mixed with water, for example by the end user, and is ready to be used or applied in its diluted liquid form.

[0032] Concentrated plant-protection formulation

[0033] In a first aspect, the invention relates to a concentrated plant-protection formulation comprising a solvent according to formula (A). In a further preferred embodiment, the concentrated plant-protection formulation further comprises an active plantprotection product.

[0034] It is a prime objective of the present invention to overcome abovementioned disadvantages of the prior art by providing an concentrated plant-protection formulation is more ecologically suitable than currently utilized formulations. In particular, there is further need for ecologically suitable solvents which are compatible with water-insoluble agrochemical active components. In particular ecological replacements for aromatic solvents, such as Solvesso 100, Isophorone, naphta and naphthalene based solvents and the like are desired.

[0035] The inventors surprisingly found that the solvents described herein show low reproductive toxicity compared to similar 2-(alkoxymetyl)tetrahydrofuran ethers; while still having high solvency and efficacy for the target agrochemical active compounds. The formulation, concentrated, does not include significant amounts of water. Typically the water content is less than 50% by weight, advantageously less than 25% by weight. It will generally be less than 10% by weight.

[0036] In a particular embodiment, the concentrated formulation may be essentially free of water. In a further preferred embodiment, the concentrated formulation may comprise less than 10.0% water, more preferably less than 8.0% water, more preferably less than 6.0% water, more preferably less than 5.0% water, more preferably less than 4.0% water, more preferably less than 3.0% water, more preferably less than 2.0% water, more preferably less than 1.0% water, more preferably less than 0.5% water, more preferably less than 0.3% water, more preferably less than 0.1% water, more preferably less than 0.01% water. All percentages of water are by weight, relative to the weight of the formulation. A concentrated formulation essentially free of water is particularly advantageous in combination with active plant protection products which are sensitive to hydrolysis.

[0037] In a preferred embodiment, the concentrated plant-protection formulation comprises a lipophilic phase, more preferably an aprotic lipophilic phase, wherein said lipophilic phase comprises a solvent according to formula (A). Preferably, said aprotic phase is essentially free of water. In a further preferred embodiment, said aprotic phase has a water solubility of at most 50 g / L, more preferably at most 25 g / L, more preferably at most 10 g / L, more preferably at most 5 g / L, more preferably at most 3 g / L, more preferably at most 1.5 g / L, more preferably at most 1.0 g / L, more preferably at most 0.75 g / L, more preferably at most 0.50 g / L, as determined at a test temperature of 20°C. For example, the aprotic solvent according to formula (A), wherein R1 is n-pentyl and without any additives, exhibits a water solubility of about 3 g / L under these conditions, and the water solubility of said solvents decreases as the R1 alkyl chain length increases. In a further preferred embodiment, the concentrated plant-protection formulation is an emulsion comprising an aqueous phase and a lipophilic phase, wherein said lipophilic phase comprises the solvent according to formula (A). More preferably, the concentrated plant-protection formulation is in the form of an emulsion-in-water (EW), microemulsion (ME), concentrated emulsion (CE), suspo-emulsion (SE), oil dispersion (OD), or emulsion concentrate (EC). These formulation types are well known in the field of plant protection and are typically selected based on the active ingredient, desired release properties, and application equipment. These preferred formulation types offer several advantages. First, the actives preferably utilized in combination with the solvents described herein, such as triazoles (e.g. tebuconazole), dinitroanilines (e.g. trifluralin), and strobilurins (e.g. azoxystrobin), exhibit poor miscibility and solubility in water. A lipophilic and aprotic continuous or dispersed phase ensures compatibility with such actives, while also avoiding the need for toxic or aromatic solvents, thus fulfilling the ecological and regulatory aims of the present disclosure. Secondly, the low water-miscibility of the solvent phase improves the emulsion's physical integrity. Specifically, it enhances the long-term storage stability of the concentrated formulation by minimizing solvent migration, droplet coalescence, Ostwald ripening, and phase inversion phenomena. As such, the use of the low-solubility aprotic solvent phase directly supports the development of robust, high-performance emulsions in line with current agronomic and environmental requirements.

[0038] In a preferred embodiment, the solvent according to formula (A) is used as a solvent in a composition comprising an active plant-protection product. More preferably, said active plant-protection product is dissolved in a liquid phase comprising said solvent according to formula (A). Even more preferably, said liquid phase essentially consists of the solvent according to formula (A), with the exception of the active plantprotection product and optionally minor formulation aids. In a further preferred embodiment, said liquid phase forms the bulk of the concentrated plant-protection formulation. Alternatively, the liquid phase may constitute a discrete component of a multiphase formulation, such as an emulsion, dispersion, or suspo-emulsion. In all such embodiments, it is preferred that the active plant-protection product is primarily dissolved in the liquid phase comprising, and preferably consisting of, the solvent according to formula (A), irrespective of the nature or composition of the other phase(s), if present. The advantages of this embodiment are multifold and align closely with the objectives of the present disclosure. The solvents according to formula (A) exhibit excellent solvency characteristics toward poorly water-soluble actives such as triazoles (e.g., tebuconazole), dinitroanilines (e.g., pendimethalin), and strobilurins (e.g., pyraclostrobin), allowing these actives to be stably and completely solubilized. Utilizing a defined solvent phase ensures reproducible formulation performance and avoids the complications of partial solubilization or crystalline precipitation during storage or dilution. This contributes to both physical stability and application reliability. Additionally, the ability to use the solvent phase either as the main formulation matrix or as a defined compartment in a multiphase system allows for broad flexibility in designing emulsifiable concentrates (EC), microemulsions (ME), concentrated emulsions (CE), suspo-emulsions (SE), or oilbased dispersions (OD). Finally, as the solvent according to formula (A) is aprotic, biodegradable, and derived in part from renewable feedstocks, its use supports a more sustainable and regulatory-compliant replacement for traditional toxic aromatic solvents while maintaining or improving performance benchmarks for agrochemical delivery.

[0039] Advantageously, the solvents of present application are aprotic, which is advantageous for the stability of certain active plant protection products compared to protic solvents as well as formulations which contain water. While typically the formulation is still diluted with water prior to use, the shelf life of the concentrated formulation is significantly increased.

[0040] The formulation is preferably a liquid formulation. In a further preferred embodiment, the concentrated formulation is preferably a liquid formulation, for example in the form of an emulsifiable concentrate (EC), dispersible concentrate (DC) or an oil-dispersion type formulation (OD). By "oil- dispersion type" it has to be understood that the fluid used as a continuous phase that can be water-immiscible or water-miscible. In this case it preferably comprises less than 500 g / L of water, more preferably less than 250 g / L. It will generally be less than 100 g / L.

[0041] The scope of the invention does not exclude the production of solid Concentrated plant-protection formulations, such as formulations in which a liquid comprising the Concentrated plant-protection formulation is supported by a mineral and / or dispersed in a solid matrix. In this case we thus obtain a wettable powder (WP) and when granulated we obtain water-dispersible granules (WDG) or water soluble granules (WSG) or water emulsifiable granule (WEG).

[0042] The formulation can of course include other ingredients (or "other additives") than the active phytosanitary product, the solvent(s), the optional emulsifying agent(s) and the optional water. It may in particular comprise viscosity modifiers, antifoam agents, in particular silicone antifoams, anti-rebound agents, anti-leaching agents, inert fillers, in particular mineral fillers, anti-freeze agents, etc.

[0043] Concentrations of the different components of the composition

[0044] The concentrated plant- protection formulation according to the invention comprises advantageously at least 1 % by weight, preferably at least 5% by weight, more preferably at least 10% by weight of said active plant-protective product relative to the total weight of the concentrated plant-protection formulation.

[0045] The concentrated plant-protection formulation may advantageously comprise: a) from 10 percent to 80 percent, preferably 20 percent to 60 percent by weight, of solvent according to the invention, relative to the total weight of the concentrated plant-protection formulation; b) from 1 percent to 80 percent, preferably 10 percent to 60 percent by weight, of active plant-protection product, relative to the total weight of the concentrated plant-protection formulation, c) from 5 percent to 50 percent, preferably 10 percent to 35 percent by weight, of surfactants, relative to the total weight of the concentrated plantprotection formulation, d) optionally, from 0 percent to 10 percent, preferably 1 percent to 5 percent by weight, of rheological additives / thickeners, relative to the total weight of the concentrated plant-protection formulation, e) optionally, from 0 percent to 25 percent, preferably 5 percent to 20 percent by weight, of wetting / dispersing agent different from the surfactant system according to the invention, relative to the total weight of the concentrated plant-protection formulation, f) from 0 percent to 10 percent, preferably 0 percent to 5 percent and more preferably less than 1 percent by weight of water.

[0046] In the following sections, each of these components as well as their more preferred embodiments be detailed. It is clear that combinations of the more preferred embodiments are particularly desired and envisioned herein; even more so the preferred combinations of solvents and their most compatible active phytosanitary products.

[0047] A) Solvent

[0048] By solvent in the phytosanitary formulation (or in the diluted composition) is meant an effective mixture, suitable to combine with the active plant-protective product. Preferably, said effective mixture is clear and stable.

[0049] The invention relates to a concentrated plant-protection formulation comprising a solvent in accordance with formula (A).

[0050] In an embodiment R1 is an alkyl group, preferably a C2 to C20 alkyl, more preferably a C4 to C20 alkyl, more preferably a C5 to C20 alkyl, more preferably a C5 to C18 alkyl, more preferably a C5 to C16 alkyl, more preferably a C5 to C14 alkyl, more preferably a C5 to C12 alkyl, more preferably a C5 to CIO alkyl, more preferably a C5 to C9 alkyl, more preferably a C5 to C8 alkyl. In a further preferred embodiment, R1 is an n-alkyl. More preferably, R1 is selected from a C5 to C12 n-alkyl, even more preferably a C5 to CIO n-alkyl, more preferably a C5 to C8 n-alkyl. More preferably, R1 is selected from n-pentyl, n-hexyl, n-heptyl and n-octyl, most preferably R1 is selected from n-pentyl, n-hexyl and n-heptyl.

[0051] The IUPAC names for the C4 to C12-alkyl ethers of 2,2-Dimethyl-l,3-dioxolane-4- methanol (glycasol) are shown below.

[0052] Alkyl Chain Length IUPAC Name

[0053] C4 (Butyl) 4-Butyloxymethyl-2,2-dimethyl-l,3-dioxolane

[0054] C5 (Pentyl) 4-Pentyloxymethyl-2,2-dimethyl-l,3-dioxolane

[0055] C6 (Hexyl) 4-Hexyloxymethyl-2,2-dimethyl-l,3-dioxolane

[0056] C7 (Heptyl) 4-Heptyloxymethyl-2,2-dimethyl-l,3-dioxolane

[0057] C8 (Octyl) 4-Octyloxymethyl-2,2-dimethyl-l,3-dioxolane

[0058] C9 (Nonyl) 4-Nonyloxymethyl-2,2-dimethyl-l,3-dioxolane

[0059] CIO (Decyl) 4-Decyloxymethyl-2,2-dimethyl-l,3-dioxolane

[0060] Cll (Undecyl) 4-Undecyloxymethyl-2,2-dimethyl-l,3-dioxolane

[0061] C12 (Dodecyl) 4-Dodecyloxymethyl-2,2-dimethyl-l,3-dioxolane

[0062] Advantageously, the solvent shows the following characteristics: can be produced fully or in high parts from renewable resources; - good solvency for the agrochemical active components, particularly those described herein and traditionally dissolved in aprotic, often aromatic, solvents;

[0063] - aprotic, better solvency and stability of concentrated formulation for desirable phytosanitary active compounds as compared to 2,2-Dimethyl- l,3-dioxolane-4-methanol and its esters, in particular when combined with common commercial triazoles and dinitroanilines;

[0064] - good adjuvant properties, such as leaf penetration, distribution / spreading and droplet behavior, low VOC emissions, high flash point and boiling point, biodegradable, and low toxicity profile, including low reproductive toxicity as compared to 2- ( a I koxy m ety I ) tet ra h yd rof u ra n et h e rs ;

[0065] B) Active plant protection product

[0066] Active phytosanitary products, in particular non-water-soluble and solid products, are known to those skilled in the art. The "active phytosanitary product" or "active plant protection product" can in particular be a herbicide, an insecticide, an acaricide, a fungicide, or an agent for the elimination of rodents ("rodenticide" in English), for example a rat poison.

[0067] By way of non-limiting examples of suitable active materials, mention may be made, inter alia, of Ametryne, Diuron, Linuron, Chlortoluron, Isoproturon, Nicosulfuron, Metamitron, Diazinon, Aclonifen, Atrazine , Chlorothalonil, Bromoxynil, Bromoxynil heptanoate, Bromoxynil octanoate, Mancozeb, Maneb, Zineb, Phenmedipham, Propanyl, phenoxyphenoxy series, heteroaryloxyphenoxy series, CMPP, MCPA, 2,4 - D, Simazine, the active products of the imidazolinone series, the organophosphate family, with in particular Azinphos-ethyl, Azinphos-methyl, Alachlor, Chlorpyriphos, Diclofop-methyl, Fenoxaprop-p -ethyl, Methoxychlor, Cypermethrin, Fenoxycarb, cymoxanil, chlorothalonyl, Ikes insecticides neonicotinoids, the family of triazole fungicides such as azaconazole, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxyconazole, fenbuconazole, flusilazole, myclobutanyl, tebucona zole, triadimefon, triadimenol, strobilurins such as pyraclostrobin, picoxystrobin, azoxystrobin, famoxadone, kresoxym-methyl and trifloxystrobin, solfonylureas such as bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, metsulfuron-methyl, nicosulfuron, sulfomethuron-methyl, triasulfuron, tribenuron-methyl. The waterinsoluble products are chosen from this list.

[0068] In a preferred embodiment, the active plant protection product is selected from the list of : chlortoluron, aclonifen, atrazine, bromoxynil, bromoxynil heptanoate, bromoxynil octanoate, propanil, phenoxyphenoxy series, heteroaryloxyphenoxy series, organophosphate family (in particular chlorpyrifos, dimethoate), azinphos- ethyl, flusilazole, azoles (in particular tebuconazole, triadimenol), triadimefon, pyraclostrobin, picoxystrobin, azoxystrobin, famoxadone, kresoxim-methyl, trifloxystrobin, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, sulfomethuron-methyl, alachlor, alpha-cypermethrin, phenmedipham, pendimethalin, trifluralin, oxyfluorfen, imidacloprid, propoxur and mixtures of combinations thereof. These preferred active plant protection products show improved compatibility with the solvents described herein, particularly in terms of solvency and stability of the concentrated formulations.

[0069] The active phytosanitary product can in particular be chosen from azoles, preferably triazoles, preferably tebuconazole. Tebuconazole is the usual name of a compound known to those skilled in the art.

[0070] As triazoles other than tebuconazole, mention may in particular be made of the following compounds: Azaconazole; bitertanol; bromuconazole; cyproconazole; diclobutrazol; difenoconazole; diniconazole; diniconazole-M; epoxiconazole; etaconazole; fenbuconazole; fluotrimazole; fluquinconazole; flusilazole; flutriafol; hexaconazole; imibenconazole; ipconazole; metconazole; myclobutanil; penconazole; prochloraz, propiconazole; prothioconazole; quinconazole; strobulurin and analogues, simeconazole; tetraconazole; triadimefon; triadimenol; triazbutil; triflumizole, triticonazole; uniconazole; uniconazole-P.

[0071] The aforementioned triazoles are believed to be well-known compounds to those skilled in the art. For reference, the table below provides a CAS number for these substances for identification as necessary.

[0072] Compound CAS Number

[0073] Tebuconazole 107534-96-3

[0074] Azaconazole 60207-31-0

[0075] Bitertanol 55179-31-2 Bromuconazole 116255-48-2

[0076] Cyproconazole 94361-06-5

[0077] Diclobutrazol 75736-33-3

[0078] Difenoconazole 119446-68-3

[0079] Diniconazole 83657-24-3

[0080] Diniconazole-M 83657-18-5

[0081] Epoxiconazole 106325-08-0

[0082] Etaconazole 60207-93-4

[0083] Fenbuconazole 114369-43-6

[0084] Fluotrimazole 94209-55-3

[0085] Fluquinconazole 136426-54-5

[0086] Flusilazole 85509-19-9

[0087] Flutriafol 76674-21-0

[0088] Hexaconazole 79983-71-4

[0089] Imibenconazole 123462-97-1

[0090] Ipconazole 125225-28-7

[0091] Metconazole 125116-23-6

[0092] Myclobutanil 88671-89-0

[0093] Penconazole 66246-88-6

[0094] Prochloraz 67747-09-5

[0095] Propiconazole 60207-90-1

[0096] Prothioconazole 178928-70-6

[0097] Quinconazole 124495-18-7

[0098] Strobilurin Group of compounds

[0099] Simeconazole 149508-90-7

[0100] Tetraconazole 112281-77-3

[0101] Triadimefon 43121-43-3

[0102] Triadimenol 55219-65-3

[0103] Triazbutil 178928-70-6

[0104] Triflumizole 68694-11-1

[0105] Triticonazole 131983-72-7

[0106] Uniconazole 83657-22-1

[0107] Uniconazole-P 88477-37-6 In a particular preferred embodiment, said active plant-protection product is a strobilurin. Strobilurins are agricultural fungicides known to the person skilled in the art. In a more preferred embodiment, said active plant-protection product may be selected from the list of : azoxystrobin, picoxystrobin, fluoxastrobin, pyraclostrobin, kresoxim-methyl, trifloxystrobin, dimoxystrobin, fenamidone, orysastrobin.

[0108] The aforementioned strobilurins are believed to be well-known compounds to those skilled in the art. For reference, the table below provides a CAS number for these substances for identification as necessary.

[0109] Strobilurin Compound CAS Number

[0110] Azoxystrobin 131860-33-8

[0111] Picoxystrobin 117428-22-5

[0112] Fluoxastrobin 361377-29-9

[0113] Pyraclostrobin 175013-18-0

[0114] Kresoxim-methyl 143390-89-0

[0115] Trifloxystrobin 141517-21-7

[0116] Dimoxystrobin 149961-52-4

[0117] Fenamidone 161326-34-7

[0118] Orysastrobin 189744-06-2

[0119] In another preferred embodiment, the active plant protection product can be chosen from dinitroanilines. More preferably, the active plant protection product is selected from preferably said plant protection product is selected from: trifluralin, oryzalin, pendimethalin, benefin, ethalfluralin, prodiamine and combinations or mixtures thereof. Most preferably said plant-protection product is selected from pendimethalin or trifluralin.

[0120] The aforementioned strobilurins are believed to be well-known compounds to those skilled in the art. For reference, the table below provides a CAS number for these substances for identification as necessary.

[0121] Compound CAS Number

[0122] Trifluralin 1582-09-8

[0123] Oryzalin 19044-88-3

[0124] Pendimethalin 40487-42-1 Benefin 1861-40-1

[0125] Ethalfluralin 55283-68-6

[0126] Prodiamine 29091-21-2

[0127] In another embodiment, phytosanitary actives which are particularly compatible with respect to solvency and stability are selected from : trifluralin, propanil, pendimethalin, dimethoate, chlorpyrifos, propoxur, oxyfluorfen, alpha- cypermethrin, alachlor, phenmedipham.

[0128] In a preferred embodiment, the active plant- protection product is selected from the group of pyridazines and pyridazones. These chemical classes include various herbicidal and fungicidal agents used in crop protection. While some members are suitable for formulation in aqueous or polar media, several others are poorly compatible with aqueous, polar, and in particular protic solvents. Many of these actives— such as pyridate and pyridachlometyl— are known to exhibit very low water miscibility and are almost completely immiscible with protic carriers such as glycols, alcohols, and glycosol-type solvents including 2,2-dimethyl-l,3-dioxolane-4- methanol. As a result, they have historically required formulation in aromatic solvents such as Solvesso 100, xylene, or other naphthalene-derived media in order to achieve sufficient dissolution and formulation stability. Surprisingly, it has now been found that the aprotic glycasol ethers disclosed herein, i.e. the solvents according to formula (A), exhibit unexpectedly high compatibility with such poorly soluble actives. In particular, these aprotic solvents enable complete solubilization of pyridate and related compounds at agriculturally relevant concentrations, forming physically stable, non-crystallizing concentrated formulations without resorting to hazardous aromatic carriers. This compatibility extends across multiple formulation types, including emulsifiable concentrates (EC), microemulsions (ME), oil dispersions (OD), and suspo-emulsions (SE), and results in both chemical and physical stability over extended storage periods.

[0129] In a preferred embodiment, the active plant-protection product is selected from pyridate, pyridachlometyl, clomazone, and fluridone. In a more preferred embodiment, the active plant-protection product is pyridate. In a further preferred embodiment, said pyridate is dissolved in a liquid phase comprising a solvent according to formula (A), preferably wherein said liquid phase consists essentially of the solvent according to formula (A). In a particularly preferred embodiment, said liquid phase forms the primary solubilizing medium of the concentrated plant- protection formulation, or forms a lipophilic phase in a multiphase system such as an emulsion or dispersion. Regardless of formulation type, it is preferred that the active plant-protection product is primarily dissolved in the solvent according to formula (A).

[0130] In a particular preferred embodiment, the concentrated plant-protection formulation comprises a solvent according to formula (A) wherein R1 is selected from a C6 to CIO alkyl, more preferably from a C7 to C8 alkyl, and most preferably wherein R1 is selected from n-heptyl or n-octyl. In a further preferred embodiment, the formulation comprises an active plant-protection product selected from the group consisting of pyridate, pyridachlometyl, clomazone, and fluridone. In a more preferred embodiment, the active plant-protection product is selected from pyridate and pyridachlometyl. In a most preferred embodiment, the formulation comprises a solvent according to formula (A) wherein R1 is n-heptyl or n-octyl, and the active plant-protection product is pyridate. This combination yields an ecologically improved, aprotic solvent system with high solvency power for pyridate, enabling its stable incorporation into concentrated formulations without the need for traditional aromatic solvents such as Solvesso or xylene. The resulting formulation, particularly in the form of an emulsifiable concentrate (EC), microemulsion (ME), or oil dispersion (OD), exhibits excellent physical stability, including reduced risk of crystallization, phase separation, or precipitation upon storage or dilution. Furthermore, the low volatility and favourable toxicological profile of the selected glycasol ethers contribute to safer handling and lower environmental impact, while maintaining the high formulation efficacy required for commercial herbicide applications.

[0131] C) Emulsifying agent

[0132] The phytosanitary formulation can comprise an emulsifying agent, typically and preferably a surfactant. Emulsifying agents are agents intended to facilitate emulsification or dispersion after bringing the formulation into contact with water, and / or to stabilize (over time and / or temperature) the emulsion or dispersion , for example by avoiding sedimentation.

[0133] Surfactants are known compounds, which generally have a relatively low molar mass, for example less than 1000 g / mol. The surfactant can be an anionic surfactant in salified or acid form, nonionic, preferably polyalkoxylated, cationic, amphoteric (term also including zwitterionic surfactants). It may be a mixture or a combination of these surfactants. By way of examples of anionic surfactants, mention may be made, without any intention of being limited thereto:

[0134] - alkylsulphonic acids, arylsulphonic acids, optionally substituted by one or more hydrocarbon groups, and in which the acid function is partially or completely salified, such as C8-C50, more particularly C8-C30, preferably C10-C22, alkylsulphonic acids, benzenesulphonic acids, naphthalenesulphonic acids, substituted by one to three C1-C30, preferably C4-C16, alkyl and / or C2-C30, preferably C4-C16, alkenyl groups.

[0135] - mono- or diesters of alkylsulphosuccinic acids, the linear or branched alkyl part of which is optionally substituted by one or more linear or branched C2- C4 hydroxylated and / or alkoxylated groups (preferably ethoxylated, propoxylated, ethopropoxylated).

[0136] - phosphate esters chosen more particularly from those comprising at least one linear or branched, saturated, unsaturated or aromatic hydrocarbon group comprising 8 to 40 carbon atoms, preferably 10 to 30, optionally substituted with at least one alkoxylated group (ethoxylated, propoxylated, ethopropoxylated). In addition, they comprise at least one phosphate ester group, mono- or di-esterified so that one or two free or partially or totally salified acid groups can be present. The preferred phosphate esters are of the type of mono- and diesters of phosphoric acid and alkoxylated (ethoxylated and / or propoxylated) mono-, di- or tristyrylphenol, or alkoxylated (ethoxylated and / or propoxylated) mono-, di- or trialkylphenol, optionally substituted with one to four alkyl groups; phosphoric acid and a C8-C30, preferably C10-C22 alkoxylated (ethoxylated or ethopropoxylated) alcohol; phosphoric acid and a C8-C22, preferably C10-C22, non-alkoxylated alcohol.

[0137] - sulphate esters obtained from saturated or aromatic alcohols, optionally substituted by one or more alkoxylated groups (ethoxylated, propoxylated, ethopropoxylated), and for which the sulphate functions are in the free acid form, or partially or totally neutralised. By way of example, mention may be made of sulphate esters obtained more particularly from saturated or unsaturated C8-C20 alcohols, which may comprise 1 to 8 alkoxylated units (ethoxylated, propoxylated, ethopropoxylated); sulphate esters obtained from polya Ikoxylated phenol, substituted by 1 to 3 saturated or unsaturated C2-C30 hydroxycarbon groups, and in which the number of alkoxylated units is between 2 and 40; sulphate esters obtained from polyalkoxylated mono-, di- or tristyrylphenol in which the number of alkoxylated units varies from 2 to 40. The anionic surfactants can be in acid form (they are potentially anionic), or in a partially or totally salified form, with a counterion. The counter-ion can be an alkali metal, such as sodium or potassium, an alkaline-earth metal, such as calcium, or even an ammonium ion of formula N(R)4+in which R, which are identical or different, represent a hydrogen atom or a Ci -C4alkyl radical optionally substituted by an oxygen atom.

[0138] As examples of nonionic surfactants, mention may be made, without the intention of being limited thereto:

[0139] - polyalkoxylated phenols (ethoxylated, propoxylated, ethopropoxylated) substituted by at least one C4 -C20 , preferably C4 - C12 , alkyl radical, or substituted by at least one alkylaryl radical, the alkyl part of which is C 1 - C6 . More particularly, the total number of alkoxylated units is between 2 and 100. By way of example, mention may be made of mono-, di- or tri(phenylethyl) polyalkoxylated phenols, or polyalkoxylated nonylphenols. Among the ethoxylated and / or propoxylated, sulfated and / or phosphated di- or tristyrylphenols, mention may be made of ethoxylated di-(l- phenylethyl)phenol, containing 10 oxyethylenated units, ethoxylated di-(l- phenylethyl)phenol , containing 7 oxyethylenated units, ethoxylated di-(l- phenylethyl)phenol, containing 7 oxyethylenated units, ethoxylated tri-(l- phenylethyl)phenol, containing 8 oxyethylenated units, tri-(l-phenylethyl) ethoxylated phenol, containing 16 oxyethylenated units, sulfated tri-(l- phenylethyl)phenol ethoxylated, containing 16 oxyethylenated units, ethoxylated tri-(l-phenylethyl)phenol, containing 20 oxyethylenated units, tri-(l-phenylethyl) phosphated ethoxylated ethyl)phenol, containing 16 oxyethylenated units.

[0140] - C 6 -C 22 alcohols or fatty acids, polyalkoxylated (ethoxylated, propoxylated, ethopropoxylated). The number of alkoxylated units is between 1 and 60. The term ethoxylated fatty acid includes both the products obtained by ethoxylation of a fatty acid with ethylene oxide and those obtained by esterification of a fatty acid with a polyethylene glycol. .

[0141] - polyalkoxylated triglycerides (ethoxylated, propoxylated, ethopropoxylated) of plant or animal origin. So suitable are triglycerides from lard, tallow, peanut oil, butter oil, cottonseed oil, linseed oil, olive oil, palm oil, grapeseed oil, fish oil, soybean oil, castor oil, rapeseed oil, coconut oil , coconut oil, and comprising a total number of alkoxylated units between 1 and 60. The term ethoxylated triglyceride refers both to the products obtained by ethoxylation of a triglyceride with ethylene oxide and to those by trans-esterification of a triglyceride with a polyethylene glycol.

[0142] - optionally polyalkoxylated (ethoxylated, propoxylated, ethopropoxylated) sorbitan esters, more particularly cyclized sorbitol esters of C 10 to C 20 fatty acids such as lauric acid, stearic acid or oleic acid, and comprising a total number of alkoxylated units between 2 and 50.

[0143] The formulation advantageously comprises at least 1%, more preferably at least 2%, more preferably at least 3%, more preferably at least 4%, more preferably at least 5%, more preferably at least 8%, by weight of dry matter, of at least one surfactant c).

[0144] Other ingredients

[0145] The Concentrated plant-protection formulation may quite obviously include certain ingredients (or "other additives") other than the herbicidal substances combination, the solvent(s), the surfactant system and the optional water. It may include, in particular viscosity modifying agents, antifoam agents and defoamers, in particular silicone antifoams and defoamers, anti-rebound agents, anti-leaching agents, inert fillers, in particular mineral fillers, anti-freeze agents, stabilizers, dyes, emetic agents, stickers (adhesion promoters), etc.

[0146] Rheological additives / thickeners

[0147] In a particular embodiment, the concentrated plant-protection formulation according to the invention may further contain rheological additives / thickeners, preferably a mineral suspending agent, more preferably selected from the group consisting of silicas, surface treated silicate, mixed oxides and mixtures thereof.

[0148] Further aspects

[0149] In a second aspect, present invention relates to the use of a concentrated plant protection product from the first aspect. In a particular embodiment, the concentrated plant protection product is used by dilution in water of the concentrated plant-protection product by mixing at least one part by weight of concentrated formulation with at least 10 parts of water, more preferably at least 100 parts of water. In a further preferred embodiment, the concentrated plant protection product is used by dilution in water of the concentrated plant-protection product by mixing at least one part by weight of concentrated formulation with at most 100 000 parts of water, more preferably at most 10 000 parts of water, most preferably at most

[0150] 1000 parts of water.

[0151] The concentrated phytosanitary formulation is intended to be spread on a cultivated field or to be cultivated, for example a soybean field, most often after dilution in water, to obtain a diluted composition. The dilution is generally carried out by the farmer, directly in a tank ("tank-mix"); for example in the reservoir of a device intended to spread the composition. It is not excluded that the operator adds other phytosanitary products, for example fungicides, herbicides, pesticides, insecticides, fertilizers. Thus, the formulation can be used to prepare a composition diluted in water of the active phytosanitary product, by mixing at least one part by weight of concentrated formulation with at least 10 parts of water, preferably less than 1000 parts. The dilution rates and quantities to be applied to the field generally depend on the phytosanitary product and the desirable dose to treat the field; this can be determined by the farm operator.

[0152] In a third aspect, the present invention relates to the diluted plant protection product, formed in accordance with the second aspect of the invention. The composition of said diluted plant protection product is as described for the first part of the invention, but with a much higher water content. As is well known in the art, this has a significant effect on the form. The diluted plant protection product is generally an aqueous composition in which the active plant protection product is dissolved or dispersed. In present case, it is typically dispersed as the preferred plant protection products have low or no water solubility.

[0153] In a particular embodiment of the third aspect, present invention relates to a consumer plant protection formulation or an off-the-shelf garden product. Consumer plant protection formulations are typically ready to use, diluted considerably compared the concentrated phytosanitary "tank mix" compositions used by farmers and professionals and often come in a different form. In a preferred embodiment, said consumer plant protection formulation is in the form of an emulsion in water or a microemulsion. Typically, the oil phase in this emulsion in water or microemulsion will be based on the solvent of formula A, further comprising an active phytosanitary product. However, significantly more water is included in ready-to-use products which leads to emulsion-in-water or microemulsions with an aqueous bulk phase. The aqueous bulk phase may further comprise additives, such as additional surfactants and fragrances. In a further preferred embodiment, the consumer plant protection formulation further comprises at least 300g water per liter of consumer plant protection formulation; more preferably at least 400 g / L of water; more preferably at least 500 g / L of water; more preferably at least 600 g / L of water; more preferably at least 700 g / L of water.

[0154] In a fourth aspect, the present invention relates to the use of said diluted plant protection product as produced according to the second aspect, or in accordance with the third aspect. In a preferred embodiment, said diluted plant protection product is used by application of said dilute plant protection product to plants, seeds, soil and I or the environment in which plants are grown.

[0155] In a preferred embodiment of the invention, the method controls phytopathogenic fungi and / or undesired vegetation and / or undesired insect or mite attack and / or for regulating the growth of plants, wherein the aforementioned composition is allowed to act on the respective pests, their environment or on the plants to be protected from the respective pest, on the soil and / or on undesired plants and / or on the crop plants and / or on their environment. In present application, particularly the protection of plants is envisioned.

[0156] In a preferred embodiment of the fourth aspect, the concentrated plant protection formulation is diluted with water, preferably in a ratio of 10 to 1000 parts of water per part of concentrated plant protection formulation; thereby forming a diluted plant protection formulation; and said diluted plant protection formulation is subsequently applied to plants or soil. In a further preferred embodiment, the diluted plant protection formulation is applied to plants or soil by spraying onto said plant or soil. In a further preferred embodiment, the diluted protection formulation is suited for direct foliar application. In a further preferred embodiment, the diluted protection formulation is suited for incorporation into the soil or (irrigation) water. Advantageously, by utilizing a more ecological solvent which is biodegradable, shows low toxicity the environmental impacts of direct and broad application of a phytosanitary formulation is minimized.

[0157] EXAMPLES

[0158] The present invention will now be further exemplified with reference to the following examples. The present invention is in no way limited to the given examples.

[0159] EXAMPLE 1: Hansen solubility parameters

[0160] Example 1 refers to the Hansen solubility parameters for the preferred C5, C6 and

[0161] C7 n-alkyl ether of glycasol as well as a range of particularly interesting phytosanitary actives. The Hansen solubility parameters are used for predicting the compatibility between compounds for the formation of a (homogeneous) solution.

[0162] Phytosanitary actives and their Hansen solubility parameters

[0163] Phytosanitary active 5D (MPa^O.5) OP (MPa^O.5) OH (MPa^O.5)

[0164] Alachlor 18.0 3.2 6.7

[0165] Chlorpyrifos 17.8 4.1 5.6

[0166] Alpha-Cypermethrin 17.5 2.6 7.4

[0167] Phenmedipham 17.6 7.1 9.4

[0168] Propanil 18.2 4.5 6.2

[0169] Pendimethalin 17.9 2.7 4.1

[0170] Tebuconazole 18.6 10.3 7.1

[0171] Triadimenol 18.4 10.5 8.0

[0172] Trifluralin 18.3 6.8 5.9

[0173] Oxyfluorfen 17.2 4.3 5.1

[0174] Imidacloprid 18.5 8.9 8.4

[0175] Dimethoate 17.9 4.2 6.1

[0176] Propoxur 18.1 5.0 7.6

[0177] Preferred solvents and their Hanssen solubility parameters

[0178] R.1 length Solvent name 6D (MPaA0.5) 6P (MPaA0.5) 6H (MPaA0.5)

[0179] (Group) _

[0180] C5 (Pentyl) 1,3-Dioxolane, 2,2- 16,54 5,87 6,64 dimethyl-4-

[0181] [(pentyloxy)methyl]-

[0182] C6 (Hexyl) 1,3-Dioxolane, 4- 16,58 5,44 6,39

[0183] [(hexyloxy)methyl]-

[0184] 2,2-dimethyl-

[0185] C7 (Heptyl) 1,3-Dioxolane, 4- 16,58 5,07 6,17

[0186] [(heptyloxy)methyl]-

[0187] 2,2-dimethyl-

[0188] The flash points of these solvents is all above 82°C, up to 95°C for the C7 ether. Example 2

[0189] Trifluralin dissolves exceptionally well into the C5 ether (4-[(pentyloxy)methyl]-2,2- dimethyl-l,3-dioxolane); the C6 ether (4-[(hexyloxy)methyl]-2,2-dimethyl-l,3- dioxolane) and the C7 ether 4-[(heptyloxy)methyl]-2,2-dimethyl-l,3-dioxolane. The C5 ether was found to have highest solvency for this phytosanitary active. Example 3

[0190] Propanil dissolves exceptionally well into the C5 ether (4-[(pentyloxy)methyl]-2,2- dimethyl-l,3-dioxolane) and the C6 ether (4-[(hexyloxy)methyl]-2,2-dimethyl-l,3- dioxolane). Solvency into the C7 ether (4-[(heptyloxy)methyl]-2,2-dimethyl-l,3- dioxolane) was lower but still good. The C5 ether again showed best performance.

[0191] Example 4

[0192] Pendimethalin dissolves well into the C5 ether (4-[(pentyloxy)methyl]-2,2-dimethyl-

[0193] 1,3-dioxolane); the C6 ether (4-[(hexyloxy)methyl]-2,2-dimethyl-l,3-dioxolane) and the C7 ether 4-[(heptyloxy)methyl]-2,2-dimethyl-l,3-dioxolane. The C7 ether was found to have highest solvency for this phytosanitary active.

[0194] Example 5

[0195] Dimethoate dissolves well into the C5 ether (4-[(pentyloxy)methyl]-2,2-dimethyl-

[0196] 1,3-dioxolane); the C6 ether (4-[(hexyloxy)methyl]-2,2-dimethyl-l,3-dioxolane) and the C7 ether 4-[(heptyloxy)methyl]-2,2-dimethyl-l,3-dioxolane. The C7 ether was found to have highest solvency for this phytosanitary active.

[0197] Example 6

[0198] Chlorpyrifos dissolves well into the C5 ether (4-[(pentyloxy)methyl]-2,2-dimethyl-

[0199] 1,3-dioxolane); the C6 ether (4-[(hexyloxy)methyl]-2,2-dimethyl-l,3-dioxolane) and the C7 ether 4-[(heptyloxy)methyl]-2,2-dimethyl-l,3-dioxolane. The C7 ether was found to have highest solvency for this phytosanitary active.

[0200] Example 7

[0201] Propoxur dissolves well into the C5 ether (4-[(pentyloxy)methyl]-2,2-dimethyl-l,3- dioxolane); the C6 ether (4-[(hexyloxy)methyl]-2,2-dimethyl-l,3-dioxolane) and the C7 ether 4-[(heptyloxy)methyl]-2,2-dimethyl-l,3-dioxolane. The C7 ether was found to have highest solvency for this phytosanitary active.

Claims

CLAIMS1. Concentrated plant-protection formulation, comprising: a) a solvent according to formula (A),wherein R1 is selected from a C5 to C12 alkyl; and b) an active plant-protection product.

2. Concentrated plant-protection formulation according to claim 1, wherein R1 is selected from a C5 to C12 n-alkyl.

3. Concentrated plant-protection formulation according to any of claims 1-2, wherein R1 is selected from a C5 to CIO n-alkyl.

4. Concentrated plant-protection formulation according to any of claims 1-3, wherein R1 is selected from a C5 to C8 n-alkyl.

5. Concentrated plant-protection formulation according to any of claims 1-4, wherein R1 is n-pentyl.

6. Concentrated plant-protection formulation according to any of claims 1-5, wherein R1 is n-hexyl.

7. Concentrated plant-protection formulation according to any of claims 1-6, wherein R1 is n-heptyl.

8. Concentrated plant-protection formulation according to any of claims 1-7, wherein the active plant-protection product is a herbicide, an insecticide, an acaricide, a rodenticide or a fungicide.

9. Concentrated plant-protection formulation according to any of claims 1-8, wherein said concentrated plant-protection formulation is in the form of an emulsifiable concentrate, a concentrated emulsion or a microemulsion; preferably comprising less than 500 g / L of water.

10. Concentrated plant-protection formulation according to any of claims 1-9, wherein said formulation comprises less than 10 wt.% of water, morepreferably less than 5 wt.% of water, more preferably less than 1 wt.% of water, relative to the weight of the formulation.

11. Concentrated plant-protection formulation according to any of claims 1-10, wherein said formulation further comprises c) a surfactant, the surfactant being chosen from nonionic surfactants, anionic surfactants and amphoteric surfactants, and mixtures or combinations thereof.

12. Concentrated plant-protection formulation according to any of claims 1-11, wherein the plant protection product is chosen from the following compounds: alachlor, chlorpyriphos, alpha-cypermethrin, phenmedipham, propanil, pendimethalin, azoles, preferably triazoles, preferably tebuconazole, triadimenol, trifluralin, oxyfluorfen, imidacloprid, dimethoate, and propoxur.

13. Concentrated plant-protection formulation according to any of claims 1-12, wherein the plant protection product is a triazole, preferably the plantprotection product is selected from the following compounds : Azaconazole; bitertanol; bromuconazole; cyproconazole; diclobutrazol; difenoconazole; diniconazole; diniconazole-M; epoxiconazole; etaconazole; fenbuconazole; fluotrimazole; fluquinconazole; flusilazole; flutriafol; hexaconazole; imibenconazole; ipconazole; metconazole; myclobutanil; penconazole; prochloraz, propiconazole; prothioconazole; quinconazole; strobulurin and analogues, simeconazole; tebuconazole; tetraconazole; triadimefon; triadimenol; triazbutil; triflumizole, triticonazole; uniconazole; uniconazole-P and mixtures of combinations thereof; most preferably said plant-protection product is tebuconazole.

14. Concentrated plant-protection formulation according to any of claims 1-12, wherein the plant protection product is a dinitroaniline, preferably said plant protection product is selected from: trifluralin, oryzalin, pendimethalin, benefin, ethalfluralin, prodiamine and combinations or mixtures thereof; most preferably said plant-protection product is selected from pendimethalin or trifluralin.

15. Use of the formulation according to one of the preceding claims, for preparing a composition diluted in water of the active plant-protection product, by mixing at least one part by weight of concentrated formulation with at least 10 parts and preferably less than 1000 parts of water.

16. Consumer plant protection formulation, wherein said formulation comprises a concentrated plant-protection formulation according to claims 1 to 8, wherein said formulation is in the form of an emulsion in water or a microemulsion; preferably comprising more than 500 g / L of water.

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